The Improbable Run of Andrew Gillum

ANDREW GILLUM'S FIRST serious act of political defiance came 18 years ago when he crashed the office he's now on the cusp of occupying himself, confronting a governor by the name of Jeb Bush.

Just a 20-year-old college sophomore at the time, Gillum was one of four students who stormed the governor's office in Tallahassee and vowed to wait as long as possible to push for changes to Bush's plan to dismantle affirmative action preferences.

With hundreds of chanting students circling the rotunda outside in protest, Bush quickly granted not only a meeting, but a few substantive concessions – promising the measure would be reviewed every three years and pledging support for legislation to pay for SAT preparatory courses for disadvantaged high school kids.

Gillum emerged claiming a step in the right direction, but also unfulfilled.

"I think that we accomplished something," he told reporters afterward, adding, "Let there be no mistake. We are not satisfied with our progress."

From the start, Gillum's underdog campaign for governor of Florida was always predicated on the same unsatisfied defiance that fueled his earliest days as an activist. To those who have known and watched him closely, his gift of personal magnetism, commitment to advocacy and unyielding ambition made him destined for this moment.

And yet when his name first floated publicly as a gubernatorial candidate, he was told all the reasons it wasn't feasible.

Geography: He's from Tallahassee, one of Florida's smallest of 10 media markets and therefore one of the hardest places to gain statewide name recognition and marshall resources.

Demography: Even Democrats had never in their history nominated a black man to become the state's chief executive.

Ideology: With positions like Medicare for all, restrictions on guns and the legalization of pot, he was assumed to be too liberal for the king of all swing states and the adopted home of President Donald Trump.

So to say what he's trying to do has never been done before is not just overhyped political jargon. That he now stands as the nominal frontrunner to become the first Democrat in 24 years to win a governor's race in Florida – and the first African-American ever to do so – is uncharted territory in itself, and if he's successful, it will be one of the most consequential results of this 2018 campaign cycle. He will immediately become one of the most important Democrats in the country and regarded as an emerging national star of a party bending to the left.

"When they tell me I can't be something, they only fuel my fire," Gillum says in an interview with U.S. News from his campaign bus just days before Election Day. "When they say it's not possible, it only gives me more motivation to prove them wrong."

But now, the question in Florida is no longer if Gillum can win. In these final days, it's become: Can he lose?

"There's something Kennedyesque about Andrew. People don't really know why – they just feel good," says Gary Yordon, a television producer who helped film Gillum's first campaign commercial for Tallahassee city commissioner 15 years ago. "The last five or six candidates [Democrats] put up for governor, they've been like oatmeal – nobody to get excited about. Andrew's like steak and eggs."It's the day after the final gubernatorial debate and Gillum is on a stage inside an auditorium at Florida Memorial University, where he's lamenting the campaign's nasty devolution to an assembly of revved up black students.

"At one point, I started to feel bad for him," Gillum says to laughs. "He had my name all down his mouth . . . And then he couldn't put respect on it."

Gillum is referring to his Republican opponent, Ron DeSantis. The 40-year-old DeSantis was a three-term, Trump-cheering congressman from Jacksonville who resigned his post last month to focus wholly on the gubernatorial race, where he's been clawing from behind since August.

A sharply skilled debater, the Harvard and Yale educated DeSantis has largely centered the final weeks of his campaign around attempting to disqualify Gillum as a corrupt, tax-raising socialist who will imperil the state's growing economy and fail to keep Floridians safe. A GOP operative involved in the DeSantis campaign says the predominant theme is: "Andrew Gillum is damn scary."

But it was in the hours after he clinched the primary that DeSantis made the calamitous mistake that put him behind the eight ball. Appearing on Fox News, DeSantis warned voters not to "monkey up" the state by voting for Gillum, a charge widely perceived as a racial epithet.

No matter how it was intended, the comment set an ugly tenor for a campaign where race has been wielded in blatantly bigoted attacks by outside extremists and more obliquely in questions about Gillum's record on crime and personal ethics.

Gillum would become only the fourth African-American governor in the nation's history, following Virginia's Douglas Wilder, New York's David Paterson and Massachusetts' Deval Patrick. While he has stopped short of branding DeSantis a racist, he believes his opponent has "doubled-down on talking about race."

"There are clearly racist elements trying to help him win," Gillum says. DeSantis has accepted thousands of dollars from a Republican activist who has used the N-word to describe former President Barack Obama and has appeared at conferences that have promoted the belief that African-Americans owe their freedom to white people and that whites are actually the victims in the race war.

In the final debate, DeSantis demonstrated exasperation at being held responsible for every supporter's remarks: "How the hell am I supposed to know every single statement someone makes?"

But Gillum says he doesn't need to "call [DeSantis] a name, I just need to cite his record."

Trump, who will appear in Florida with DeSantis twice in the final week before the election, called Gillum "a thief" on Monday. And as DeSantis attacked Gillum during a rally in Coral Springs later, the crowd chanted "Lock him up!"

Gillum has clutched to varying polling leads in the preponderance of general election surveys, with a few showing his advantage as high as between five and seven points, a margin that would amount to a blowout in normally too-close-to-call Florida and unprecedented for any Democrat in memory. But in the interview, Gillum dismissed this reporter's description of him as the front-runner.

"I haven't presumed myself to be the favorite. I presumed myself to be in the fight of my life," he says. "Florida is a 1 percent state. It will likely come down to fewer than 1 percent of the votes in this state who will decide the next governor, so I've gotta go and get those votes."

Still, he adds, "I feel like we're going to win."

Susie Wiles, the chair of the DeSantis campaign says Gillum deserves his due. "He's an exciting, different kind of candidate for Florida. There becomes an early cachet around some candidates and that's what we're seeing here."

"It doesn't mean it holds to the end," she says.

Born in Miami as the fifth of seven children, Gillum grew up poor. His mother drove a school bus, pressed clothes at a dry cleaner in the summer and cleaned homes on the weekends. His father, who struggled with alcoholism, worked construction and sold fruits and vegetables on the street corner. With several of his older brothers getting in trouble with the law, his father's advice to him was that if he kept his record clean, he could be admitted to the military.

As a teenager Gillum became engrossed by the NBC show, "A Different World," a spin-off from "The Cosby Show" that featured a cast of African-American students and their lives at a fictional all-black college in Virginia. It was the first instance Gillum ever saw of people who looked like him succeeding academically, thriving socially and on the path to big careers. It changed what he thought was possible.

"In spite of the fact of my Dad telling me that if I did well, I could go to the military, I said, 'No, I want to go to college,'" he recalls.

In 1992, his family moved from Miami to Gainesville for a fresh start and to be closer to Gillum's grandparents. It is there where he met Chris Chestnut, the only other African-American in his class, whose mother was a member of the Florida legislature and the first African-American woman to be elected mayor of Gainesville.

Gillum began hanging out at Chestnut's house and steadily became immersed in political conversations prompted by Cynthia Chestnut.

"She took me under her wing and . . . I just got increasingly interested," Gillum recalls. "She had me come up to the Capitol so I could be exposed to the legislature. We were just really overexposed to the political process."

Determined to break his family's cycle of intergenerational poverty, Gillum became the first in his family to graduate high school and go on to college in Tallahassee, in part because he saw that location as where the action was happening.

Gillum ventured two and a half hours west to attend the historically black Florida Agricultural and Mechanical University, where he quickly became known as a curious and persuasive student leader. He mobilized his fellow students to protest for voting rights for people who had been removed from the official rolls and spearheaded the affirmative action meeting with Jeb Bush.

Later that same year, it was Bush's brother's narrow presidential lead in Florida that prompted another Gillum-inspired protest as a recount over hanging chads and indecipherable ballots dragged out for weeks.

"Nobody wanted to do that," recalls Melanie Newman, a classmate and friend of Gillum's at Florida A&M. "We were tired. We felt defeated. We felt like we didn't have enough of a voice. And Andrew held a meeting, he invited people who had trouble voting to share their experiences. A lot of people showed up and he put together a strategy."

"Going into the meeting, it was like, 'Oh Andrew, always trying to do something. We gotta talk him out of it.' And Andrew was always like, 'We don't have to take what they give us.'"

It soon became clear that his senior year stint as student government president and forthcoming political science degree were not merely resume-building exercises. Gillum began closely tracking the actions of the Tallahassee City Commission, which passed an ordinance limiting the number of students who could occupy a house at the same time.

Gillum saw this as housing discrimination and organized a group of students to protest the move at a meeting. He felt like some of the commissioners weren't taking them seriously.

"One commissioner said, 'Students are like house guests. We love to see you come, but can't wait to see you leave!' They broke into laughter," he recalls. "I just remember thinking, 'Oh no they didn't.' We fuel this economy and we came here to let our voices be heard and they completely disrespected us. And I decided, you know what? I'm going to take one of them out. That moment of disrespect," he pauses, "told me I had to do something about it."

Few local officials bring game-changing ideas to city hall, but Gillum was an aggressively reactive commissioner, assiduously responding to people's problems and requests. Throughout his time there, Gillum's sweet spot was his natural ability to connect with the young people. He became an unflagging force in pushing through a new city center for teenagers, often stopping in unannounced to check on middle and high school students, even though most weren't old enough to vote for him.

"One thing about Andrew is that he's been consistent. Sometimes young people lose focus or they lose interest. He's never lost interest. He's always been consistent with his time and his talents," says Kendrick Meek, a former Democratic congressman from Florida.